US Open 2025: Jenson Brooksby vs Flavio Cobolli preview, head-to-head, odds, prediction and pick

Match Details

Fixture: (24) Flavio Cobolli vs Jenson Brooksby

Date: August 27, 2025

Tournament: US Open 2025

Round: Second Round (Round of 64)

Venue: USTA Billie Jean King National Tennis Center, New York, USA

Category: Grand Slam

Surface: Outdoor hard

Prize Money: $90,000,000

Live Telecast: USA - ESPN, ESPN+ | UK - Sky Sports | Canada - TSN, RDS | India - JioHotstar

---

Jenson Brooksby vs Flavio Cobolli preview

Jenson Brooksby hits a backhand at US Open | Image Source: Getty

24th-seeded Flavio Cobolli will face the dangerous local favorite Jenson Brooksby for a place in the third round of the 2025 US Open on Wednesday (August 27).

Cobolli had initially started his season on the ATP Tour on a rough note, beginning the year by dropping nine of his first 12 on-court outings. The Italian has since righted the ship by winning his first two singles pro titles and recording his maiden Major quarterfinal result at Wimbledon.

Although there was a little more to be desired from the 23-year-old's performance during this year's North American hardcourt swing, he arrives in New York as one of the dark horses that can go far. Like his higher-ranked opponent, Brooksby has also reached two singles finals in 2025 (winning the Houston Open title and dropping the Eastbourne International title match).

In his previous four US Open main draw campaigns, the former World No. 33 had made the fourth round once (2021). The 24-year-old certainly has more experience at Flushing Meadows than the 24th seed, who reached the third round of the tournament in his first-ever main draw appearance in 2024. That said, both players' respective paths to the second round this year have been similar.

---

Jenson Brooksby vs Flavio Cobolli head-to-head

Brooksby leads Cobolli 1-0 in their head-to-head meetings on the ATP Tour. The American downed the Italian in the second round of the 2022 Italian Open in straight sets.

---

Jenson Brooksby vs Flavio Cobolli odds

Player	Moneyline	Handicap Bets	Total Games (Over/Under)
Jenson Brooksby	+130	-1.5 (+210)	Over 37.5 (-125)
Flavio Cobolli	-165	+1.5 (-325)	Under 37.5 (-115)

All bets sourced from BetMGM.

---

Jenson Brooksby vs Flavio Cobolli prediction

Flavio Cobolli hits a forehand at US Open | Image Source: Getty

During his first-round match at the US Open earlier on Monday, Brooksby saved multiple break points in the deciding set to eke out a 6-3, 6-7(4), 6-4, 3-6, 6-4 victory against Australia's Aleksandar Vukic in nearly four hours. Cobolli endured a similar outing in his New York opener as he came from a break down to beat his compatriot Francesco Passaro 7-5, 4-6, 6-4, 3-6, 6-3.

Both players will have to put together a sharper display in their respective service games when they face off on Wednesday to ensure that the match doesn't go the distance. The unseeded American can be a tricky shotmaker from the baseline, especially considering how well he disguises his two-handed backhand.

Cobolli's counteractive style of play is just as effective on the hardcourts at Flushing Meadows, meaning that he will be ready to match his older opponent during longer exchanges.

Pick: Cobolli to win in five sets.